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Synthesis of 2-Aminoquinazolinones via Carbonylative Coupling of ortho-lodoanilines and Cyanamide
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
2016 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 81, no 7, 2966-2973 p.Article in journal (Refereed) PublishedText
Abstract [en]

Herein, we describe a convenient and efficient synthesis of 2-aminoquinazolin-4(3H)-ones and N1-substituted 2-aminoquinazolin-4(1H)-ones by a domino carbonylation/cyclization process. The reaction proceeds via carbonylative coupling of readily available ortho-iodoanilines with cyanamide followed by in situ ring closure of an N-cyanobenzamide intermediate. The products were easily isolated by precipitation in moderate to excellent yields for a wide range of substrates, making this a highly attractive method for the synthesis of 2-aminoquinazolinones.

Place, publisher, year, edition, pages
2016. Vol. 81, no 7, 2966-2973 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-295556DOI: 10.1021/acs.joc.6b00249ISI: 000373520200028PubMedID: 26967689OAI: oai:DiVA.org:uu-295556DiVA: diva2:941313
Available from: 2016-06-22 Created: 2016-06-08 Last updated: 2016-06-22Bibliographically approved

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Åkerbladh, LindaOdell, Luke R.
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